36950-98-8

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-(4-hydroxyphenyl)-5,6,7,8-tetramethoxy-
• CAS NO: 36950-98-8
• Molecular Formula: C19H18O7
• Molecular Weight: 358.348
• Mol File: 36950-98-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-(4-hydroxyphenyl)-5,6,7,8-tetramethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-(4-hydroxyphenyl)-5,6,7,8-tetramethoxy-(36950-98-8)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-(4-hydroxyphenyl)-5,6,7,8-tetramethoxy-(36950-98-8)

Safety Data

• Hazardous Substances Data: 36950-98-8(Hazardous Substances Data)

Upstream product

• 3162-28-5 2-hydroxy-3,4,5,6-tetramethoxyacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 481-53-8 tangeritin 
• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 85374-52-3 1-(4-benzyloxyphenyl)-3-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)propane-1,3-dione 
• 1350827-37-0 2-(4-benzyloxybenzoyloxy)-3,4,5,6-tetramethoxyacetophenone 
• 73898-14-3 4'-benzyloxy-5,6,7,8-tetramethoxyflavanone 
• 40110-95-0 4-benzyloxy-2'-hydroxy-3',4',5',6'-tetramethoxychalcone 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 40110-96-1 4'-benzyloxy-5,6,7,8-tetramethoxyflavone 

Downstream Products

• 481-53-8 tangeritin 
• 2798-20-1 gardenin B 
• 6959-55-3 Acetic acid 4-(5,6,7,8-tetramethoxy-4-oxo-4H-chromen-2-yl)-phenyl ester 
• 16545-23-6 xanthomicrol 

Relevant articles and documents

Tangeretin inhibits the proliferation of human breast cancer cells via CYP1A1/CYP1B1 enzyme induction and CYP1A1/CYP1B1–mediated metabolism to the product 4′ hydroxy tangeretin

Tangeretin is a polymethoxylated flavone with multifaceted anticancer activity. In the present study, the metabolism of tangeretin was evaluated in the CYP1 expressing human breast cancer cell lines MCF7 and MDA–MB–468 and in the normal breast cell line M

Analysis of Fluorescence Spectra of Citrus Polymethoxylated Flavones and Their Incorporation into Mammalian Cells

Citrus polymethoxylated flavones (PMFs) influence biochemical cascades in human diseases, yet little is known about how these compounds interact with cells and how these associations influence the actions of these compounds. An innate attribute of PMFs is their ultraviolet-light-induced fluorescence, and the fluorescence spectra of 14 PMFs and 7 PMF metabolites were measured in methanol. These spectra were shown to be strongly influenced by the compounds' hydroxy and methoxy substituents. For a subset of these compounds, the fluorescence spectra were measured when bound to human carcinoma Huh7.5 cells. Emission-wavelength maxima of PMF metabolites with free hydroxyl substituents exhibited 70-80 nm red shifts when bound to the Huh7.5 cells. Notable solvent effects of water were observed for nearly all these compounds, and these influences likely reflect the effects of localized microenvironments on the resonance structures of these compounds when bound to human cells.

Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase

Aromatic peroxygenases are extracellular fungal biocatalysts that selectively oxidize a variety of organic compounds. We found that the peroxygenase of the fungus Agrocybe aegerita (AaeAPO) catalyzes the H 2O2-dependent hydroxylation of diverse flavonoids. The reactions proceeded rapidly and regioselectively yielding preferentially monohydroxylated products, e.g., from flavanone, apigenin, luteolin, flavone as well as daidzein, quercetin, kaempferol, and genistein. In addition to hydroxylation, O-demethylation of fully methoxylated tangeretin was catalyzed by AaeAPO. The enzyme was merely lacking activity on the quercetin glycoside rutin, maybe due to sterical hindrance by the bulky sugar substituents. Mechanistic studies indicated the presence of epoxide intermediates during hydroxylation and incorporation of H2O2-derived oxygen into the reaction products. Our results raise the possibility that fungal peroxygenases may be useful for versatile, cost-effective, and scalable syntheses of flavonoid metabolites.